Toluene → N-(2-Naphthylmethyl)phthalimidine

HRID 2427552Notes

Reaction equation

HRID 2427552 reaction equation
[CH:1]1[C:10]2C(=CC=CC=2)C=C[C:2]=1[NH:11]C.CO[C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[CH2:22]Br.[C:25]([O-:28])([O-])=O.[K+].[K+].C(OCC)(=O)C.[C:37]1([CH3:43])[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>>[CH:22]1[C:17]2[C:16](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:15]=[CH:10][C:1]=1[CH2:2][N:11]1[CH2:43][C:37]2[C:42](=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:25]1=[O:28]

Participants

6

Reactant 5

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 1375052-Naphthalenamine, N-methyl-HCID 2734813Methyl 2-(bromomethyl)benzoate

Product 1

HCID 182329N-(2-Naphthylmethyl)phthalimidineYield 70%

Conditions

Temperature
100 °C

Procedure

A mixture of naphthalen-2-yl-methylamine (47.2 mg, 0.3 mmol), 2-bromomethyl-benzoic acid methyl ester (68.7 mg, 0.3 mmol), and K2CO3 (83 mg, 0.6 mmol) in toluene (2 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using a gradient of hexanes to 50% ethyl acetate in hexanes afforded 2-naphthalen-2-ylmethyl-2,3-dihydroisoindol-1-one (57 mg, 70%). GC/MS gave: m/z (rel.int.) 273 (M+, 45), 141 (100), 119 (27), 115 (27), and 91 (25).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-4a2ea03810ab4027930d8aac32bcba38
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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